The Stacking Benjamins Show: How to Build a Financial Plan That Holds Up When Life Doesn't (SB1818)

Release Date: March 20, 2026
Hosts: Joe Saul-Sehy, Paula Pant, OG (absent, replaced by guest Paul Merriman), Jesse Kramer
Guest Expert: Paul Merriman
Theme: Building "All Weather" financial plans and portfolios that can withstand life's unpredictable challenges.

Episode Overview

This episode dives into the concept of building an "all weather" financial plan—one that endures market swings, economic shocks, personal setbacks, and everything in between. The hosts, along with special guest Paul Merriman (respected investor and educator), unpack the psychology of chasing "shiny" high-return investments versus building robust, resilient money systems. They discuss asset allocation, risk management, behavioral pitfalls, and the practical steps you can take to make your finances stormproof.

Key Discussion Points & Insights

1. Why Do We Chase Shiny Investments? ([14:58–19:24])

• Paula Pant: Discusses the allure of flashy investments—just like sports cars symbolize success, hot assets (like crypto or AI stocks) become shortcuts in our minds for financial success. The stories of big wins reinforce this mindset, despite survivorship bias.
• Jesse Kramer: Emphasizes the role of comparison and benchmarking. Many investors measure their performance against headlines (e.g., the S&P 500) without considering if those benchmarks are relevant to their goals.
  • Quote: "If you're about to retire and your portfolio...is 60/40, and you're comparing yourself to the S&P 500, that's a benchmarking issue..." (17:10)
• Paul Merriman: Warns of the dual dangers: people taking too much risk chasing past winners and people being too afraid to take any risk.

2. Risks of Chasing Trends & the 'Lottery Ticket' Mentality ([19:24–22:11])

• Paul Merriman: Even when someone wins with a risky bet or the lottery, it’s a bad lesson. Teaching the next generation to count on those “lottery ticket” moments is damaging.
  • Quote: "The worst thing to do is to teach a kid how to play the stock market game in high school, and he wins. Now they think the way to invest is the way that stock market game turned out. That’s a terrible lesson." (20:11)
• Paula Pant: Differentiates between leaning into genuine society-changing trends (like the Internet or AI) and attempting to pick specific winners, which is near impossible.

3. Defining & Building an 'All Weather' Portfolio ([22:31–27:05])

• Jesse Kramer: Explains the Ray Dalio “All Weather” approach—diversification across asset classes (stocks, bonds, gold, commodities) to withstand macroeconomic risks (inflation, deflation, recession, etc.).
• Paul Merriman: Shares his approach—diversified "ten fund strategy" split evenly across US/international, large/small, value/growth equities, and a balanced stock/bond allocation (50/50). Notes the biggest risk: market timing, not asset selection.
  • Quote: "The problem is when people start market timing...when they start moving to international, typically the time they move is when it's been on a run already." (25:49)
• Paula Pant: Explains how indexes "self-clean." As winners grow, you own more of them, and as companies fade, they're gradually replaced—no hand-weeding required.

4. All Weather Money: Beyond Portfolios ([27:05–30:44])

• Cash & Flexibility: Paula hammers the importance of emergency cash, insurances, and overall financial 'defense.' People often resent cash yields during bull markets, but regret not having reserves during downturns.
  • Quote: "Cash is king, right? Nothing is more important than it." (27:43)
• Behavioral Defense: Jesse highlights the need for introspection about risk and understanding the threats unique to your situation, not just focusing on market doom scenarios.

5. Risk Tolerance & Investor Psychology ([30:44–34:16])

• Paul Merriman: Argues every investor should build their plan as though a bear market starts tomorrow and be emotionally/financially prepared to lose a sizeable portion of their portfolio.
  • Quote: "Every person...should all expect that tomorrow starts the worst bear market in their life. They should be built from day one to expect bad things." (31:16)
• Risk Management: Disability and unforeseen life shocks are often neglected but can have devastating effects. Paul stresses adequate insurance and risk assessment beyond just portfolio returns.

6. Biggest Retirement Shocks & Withdrawal Pitfalls ([51:17–53:59])

• Paul Merriman: The biggest real-life financial shocks he's seen weren't market-related but due to being underinsured (e.g., post-accident lawsuits) or overspending (withdrawal rates of 6-7%+).
  • Quote: "The biggest one I saw was being underinsured and getting in a car accident...it wiped them out. They didn't have the umbrellas that they needed." (51:17)
• Illusions of Safety: Many overestimate safe withdrawal rates by assuming unrealistic future returns, leading to running out of money.

7. Coping With Job Loss & AI Anxiety ([54:49–56:40])

• Jesse Kramer: Emergency funds offer a practical if temporary buffer. Consider skills less susceptible to automation, and always have a networking/resume back-up plan. Thinking ahead about fallback options is crucial.

• Paula Pant: Underscores the importance of negotiation skills—not as confrontation, but collaborative problem solving. Negotiate on many fronts (salary, benefits, flexibility), and understand what matters to the other party.

8. Behavioral Biases and The Danger of Chasing Winners ([59:16–66:37])

• Paul Merriman: Discusses "recency bias"—the tendency to assume what's hot now will stay hot and the related danger of abandoning diversification for flashy returns. Advising is as much about stopping people from making mistakes as it is about choosing investments.
  • Quote: "One market timing mistake can cut your retirement in half for a lifetime—one." (61:53)
• Jesse Kramer: Shares a client story—panic-selling at the market's bottoms (e.g., COVID-19 crash) leaves "scars" on portfolios that can never be reversed.
• Doug: The "crash the plane" exercise—deliberately list everything that could ruin your plan, then simply don’t do those things.

Notable Quotes & Memorable Moments

• Paul Merriman: "Every person should expect that tomorrow starts the worst bear market in their life." (31:16)
• Paula Pant: "Cash is king, right? Nothing is more important than it." (27:43)
• Jesse Kramer: "If we wanted to screw this up as royally as we possibly could to make sure this plane crashes, ... there are so many things. Then all you do... is just put ‘don’t’ in front of that." (63:29)
• Paul Merriman: "One market timing mistake...can cut your retirement in half for a lifetime." (61:53)
• Paula Pant: "Negotiation is a form of creative collaboration." (58:01)
• Paula Pant: On behavioral finance: "Your beliefs shape your reality." (69:47)

Timestamps for Major Segments

• Shiny Investments & Their Psychology: 14:58–22:11
• All Weather Portfolio Definitions & Strategies: 22:31–27:05
• All Weather Money: Cash, Flexibility, Insurance: 27:05–34:16
• Trivia Segment (skip): 34:16–51:17
• Biggest Retirement Shocks & Withdrawal Issues: 51:17–53:59
• Job Loss & AI-Proofing Your Career: 54:49–56:40
• Negotiation As a Key Defensive Skill: 56:40–58:12
• Behavioral Biases & Avoiding Costly Mistakes: 59:16–66:37

Final Takeaways

• Preparation for Downturns: Always plan for the worst-case scenario—whether it’s in your portfolio or your life.
• Prevention Over Prediction: Diversification, risk assessment, and behavioral discipline are more effective than trying to pick winners or time the market.
• Defense Matters: Emergency reserves, adequate insurance (especially umbrella and disability), and careful withdrawal rates are foundational.
• Behavioral Mastery: Know the psychological traps—recency bias, overconfidence, envy—and actively guard against impulsive moves.
• Holistic Strategy: An all-weather financial plan is about more than investments; it’s about defense, flexibility, adaptability, and having the skills to negotiate your way through storms.

Discover More

• Paul Merriman’s Boot Camp: Free, comprehensive educational resources on building resilient portfolios (paulmerriman.com).
• Afford Anything Podcast (Paula Pant): Upcoming episodes on behavioral finance and the psychology of money.
• Personal Finance for Long-Term Investors Podcast (Jesse Kramer): Recent episode on Monte Carlo simulation for retirement planning.